PornPorn Transgender • US
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    Dating
    Subscriptions
    • Upload
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Sissy
    • Shemale Fucks Girl
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Anal Machine Fuck Training Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Anal
    Fuck
    Training
    Machine
    Sissy Fuck Machine
    Anal Fuck Machine
    Sissy Anal Fuck
    Sissy Fucked
    Sissy Anal
    Fucking Machine
    Anal Sissy
    Fuck Sissy
    Machine Fuck
    Anal Fuck
    Sissy Crossdresser
    Femboy Fucked
    Sissy Feminization
    Crossdresser Fucked
    Sissy BBC
    Best Videos
    By clicking the content you will also see an ad. AD
    I'll fill your asshole with cum to overflowing
    06:01
    I'll fill your asshole with cum to overflowing
    MrNastyXavier
    2M views
    Sissy Slut Sloppy Deepthroat and Anal Fuck Training in Hotel
    02:27
    Sissy Slut Sloppy Deepthroat and Anal Fuck Training in Hotel
    Foxxy Pink
    7.6K views
    How to train your sissy ass
    17:41
    How to train your sissy ass
    663.8K views
    Spandexfemboy - Psychodelic Sissy Anal Fuck
    16:26
    Spandexfemboy - Psychodelic Sissy Anal Fuck
    FapHouse
    3K views
    Fucking of a Lifetime - Variety Itsol
    10:36
    Fucking of a Lifetime - Variety Itsol
    Rodrigo Amor
    3.4M views
    Sissy Anal Compilation
    14:49
    Sissy Anal Compilation
    FapHouse
    1.6K views
    sissy training
    39:53
    sissy training
    136K views
    Sissy anal destruction with huge dildo fucking machine
    04:11
    Sissy anal destruction with huge dildo fucking machine
    AngelSissyWhore
    2.3K views
    Lena Vesper's Milking & Gooning Session
    08:12
    Lena Vesper's Milking & Gooning Session
    FapHouse
    209.7K views
    Femboy Sissy Anal Webcam Show
    01:39
    Femboy Sissy Anal Webcam Show
    G8pess
    3.7K views
    Shemale Anatomy
    03:06
    Shemale Anatomy
    2.8M views
    20mins casual sissy anal reaming training on the fuck machine - non stop fuck cd whore
    23:00
    20mins casual sissy anal reaming training on the fuck machine - non stop fuck cd whore
    Jasmine_dlight
    5.6K views
    3 anal orgasm and hot creampie for skinny trans whore
    16:52
    3 anal orgasm and hot creampie for skinny trans whore
    ActorFab
    2M views
    Intense Sissy Anal Fuckmachine Training
    05:17
    Intense Sissy Anal Fuckmachine Training
    FapHouse
    9.4K views
    Sissy #2: Becoming A Cock Slut
    15:35
    Sissy #2: Becoming A Cock Slut
    873.6K views
    Sissy anal training in chastity with a fucking maschine
    09:15
    Sissy anal training in chastity with a fucking maschine
    4.3K views
    Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
    10:16
    Chastity Sissygasm Guide How to Cum From Anal In a Cock Cage
    Jessica Bloom
    76.4K views
    Sissy anal training at the hotel
    13:03
    Sissy anal training at the hotel
    FrivolousStage1
    3.7K views
    Another straight boy turned by Elizabeth Stewart
    04:05
    Another straight boy turned by Elizabeth Stewart
    Elizabeth Stewart
    3.1M views
    Sissy anal training
    08:21
    Sissy anal training
    FumikoKatt
    4.5K views

    Relevant Short videos

    Stretched Out in Chastity
    Stretched Out in Chastity
    Roxie Black
    11K views
    Trans on a Fuckmachine for Her Neighbor
    Trans on a Fuckmachine for Her Neighbor
    Emmy Angeles
    1.9K views
    I start my fucking machine to train my sissy boipussy
    I start my fucking machine to train my sissy boipussy
    ManonTrav67
    2.5K views
    Emmysdesire's Anal Training Before Live
    Emmysdesire's Anal Training Before Live
    Emmysdesire
    1.8K views
    Epic moment from "Redhead sissy first using a sex-machine. This is a sweet gift from a fan"
    Epic moment from "Redhead sissy first using a sex-machine. This is a sweet gift from a fan"
    Sonechka25
    2.1K views
    Spandexfemboy - Psychodelic Sissy Anal Fuck
    Spandexfemboy - Psychodelic Sissy Anal Fuck
    Spandexlover89
    402 views
    I turned my straight roommate into my wife
    06:06
    I turned my straight roommate into my wife
    CutePinkUnicorn
    2.2M views
    Sissy anal training part 2
    01:44
    Sissy anal training part 2
    FumikoKatt
    2.1K views
    A guide to sissication: Beginner - Am I a sissy?
    23:32
    A guide to sissication: Beginner - Am I a sissy?
    757.2K views
    Extreme Anal Gape Xxxl Dildo & Fuck Machine
    05:56
    Extreme Anal Gape Xxxl Dildo & Fuck Machine
    FapHouse
    67.8K views
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    29:33
    Trans Ria Bentley Enjoys Huge BBC Spitroast Anal Creampie
    Ria_Bentley
    2.6M views
    Sissy Evolution- A Captioned Compilation
    05:53
    Sissy Evolution- A Captioned Compilation
    Tiffany Cox
    19.4K views
    Fuck machine anal orgasm
    03:04
    Fuck machine anal orgasm
    Sissy-boys
    106.5K views
    Crossdresser gets machine fucked with XXL Monster Dildos #4
    51:27
    Crossdresser gets machine fucked with XXL Monster Dildos #4
    Niceguy_1991
    195.4K views
    Anal training for experienced anal sluts
    27:27
    Anal training for experienced anal sluts
    231.2K views
    4 Inch Wide Toy on Machine
    05:12
    4 Inch Wide Toy on Machine
    AmandaKnight
    46.6K views
    Damazonia & Natalie Mars - Anal Fisting Strapon
    15:55
    Damazonia & Natalie Mars - Anal Fisting Strapon
    299.8K views
    Sissy Elvi Lynx's asshole EATS massive Dildos
    10:01
    Sissy Elvi Lynx's asshole EATS massive Dildos
    Elvi Lynx
    8.8K views
    sissy anal cumming trainer
    56:50
    sissy anal cumming trainer
    750.2K views
    Sissy Fuck Machine Training
    07:39
    Sissy Fuck Machine Training
    FapHouse
    81K views
    Sissies Guide for Loving Anal
    05:04
    Sissies Guide for Loving Anal
    185.6K views
    Trans on a Fuckmachine for Her Neighbor
    06:44
    Trans on a Fuckmachine for Her Neighbor
    Emmy Angeles
    27.5K views
    Sissy Dreams 3
    26:07
    Sissy Dreams 3
    1.2M views
    Sissy Candy in Lingerie Gets Fucked by Her Machine with a Huge Dildo
    07:55
    Sissy Candy in Lingerie Gets Fucked by Her Machine with a Huge Dildo
    Sissy Candy
    46.8K views
    anal orgasm training
    10:17
    anal orgasm training
    155.4K views
    Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll
    08:25
    Sissy Candy in Red Lingerie Gets Spitroasted by Her Fucking Machine and Doll
    Sissy Candy
    21.5K views
    Self Suck Cum in Mouth With Fucking Machine! - Jessica Bloom
    07:15
    Self Suck Cum in Mouth With Fucking Machine! - Jessica Bloom
    linktree
    232.9K views
    Sissy in Pink Dress and Chastity Plays with Her Butt Plug and Gets Fucked Hard by Machine
    16:04
    Sissy in Pink Dress and Chastity Plays with Her Butt Plug and Gets Fucked Hard by Machine
    FapHouse
    16.1K views
    My wife told me to play this
    11:13
    My wife told me to play this
    970.6K views
    Sissy in Black Lingerie Gets Fucked by Her Fucking Machine
    39:50
    Sissy in Black Lingerie Gets Fucked by Her Fucking Machine
    Sissy Candy
    3.9K views
    Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum
    07:12
    Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum
    Jessica Bloom
    201.2K views
    Just my deep Belly Bulge training
    01:49
    Just my deep Belly Bulge training
    Miolee
    50.6K views
    Sissy #3: Feminize Yourself
    16:07
    Sissy #3: Feminize Yourself
    661.4K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Anal Machine Fuck Training

    • Femdom Anal Training for Sissy Boyfriend
    • Inserting Everyday Objects Into My Ass
    • Riding Dildo Orgasm Talking Dirty
    • Fuck Machine Extreme Fast
    • Anally Destroyed by a Big Dick Shemale
    • First Time Being Fucked as Crossdresser
    • Thrusting Butt Plug
    • Rectal Prolapse
    • Femboy Sissification
    • Huge Insertions
    • Multiple Continuous Cum 10 Times
    • Beautiful Sexy Video XXX
    • Trans Chastity Cages
    • Oh No No No No
    • Fucking Sex Toy
    • Amateur Sissygasm
    • Urethra Torture
    • Shoulder Deep Fisting
    • Public Buttplug
    • Brutal BBC Fucks CD
    xHamster
    • Press
    • Blog
    • Creator's Blog
    • Advertising
    • xHamster Awards 2025
    Help
    • FAQ
    • Contact us
    • Content Removal
    • Improve xHamster
    Legal
    • Terms of use
    • Privacy policy
    • Cookies policy
    • DMCA/Copyright
    • Parental Controls
    • EU DSA
    • Trust and Safety
    Start making money with us
    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile Version
    18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement
    RTA Restricted To AdultsRTA Restricted To Adults
    xHamster is adults only website!

    The content available on xHamster may contain pornographic materials.

    xHamster is strictly limited to those over 18 or of legal age in your jurisdiction, whichever is greater.

    One of our core goals is to help parents restrict access to xHamster for minors, so we have ensured that xHamster is, and remains, fully compliant with the RTA (Restricted to Adults) code. This means that all access to the site can be blocked by simple parental control tools. It is important that responsible parents and guardians take the necessary steps to prevent minors from accessing unsuitable content online, especially age-restricted content.

    Anyone with a minor in their household or under their supervision should implement basic parental control protections, including computer hardware and device settings, software installation, or ISP filtering services, to block your minors from accessing inappropriate content.

    To enter xHamster you must be 18 or older
    how to protect your minors
    RTA Restricted To AdultsRTA Restricted To Adults